


The Debauchery of Miss Granger

by AbsintheDreams



Category: Harry Potter - J. K. Rowling
Genre: BDSM, Dark Tom Riddle, F/M, Pirates, Possessive Tom Riddle, Shameless Smut, Tom Riddle is His Own Warning
Language: English
Status: Completed
Published: 2020-02-23
Updated: 2020-02-23
Packaged: 2021-02-27 22:34:38
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 9,720
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22863358
Author URL: https://archiveofourown.org/users/AbsintheDreams/pseuds/AbsintheDreams
Summary: A/U: Captain Riddle has watched his little assassin for a while now. Planned her downfall meticulously. When she finally strikes, there's no longer a need for pretense or propriety. Finally. He can have her. Fulfill his dark fantasies and make his dear, proper Miss Granger beg for it.Shameless, dark, lemony smut. Pure debauchery. Most likely a one-shot. Enjoy.
Relationships: Hermione Granger/Tom Riddle
Comments: 15
Kudos: 244





	The Debauchery of Miss Granger

We never meant to be so jaded  
Never meant to fall so far  
Now all that we love is faded  
How did we let it go this far  
Feels like a dark day coming  
Hurts like a love one lost  
Only the brave aren't running  
Yet we still fear the cost

His black boots. Her tempestuously cinnamon glare. A riot of untamed curls ringed her slender shoulders, her tunic cut in a fashion that pressed her breasts against the white cotton pleasantly. Captain Riddle raised a mocking raven brow at her, noting the razor sharp steel sword she held at his jugular dismissively. Hermione didn't tremble or flinch. Her gaze and sword hand held strong. 

"You will answer for them, those deaths, I'm no posh English court. I won't be bought," she warned, teeth gritted, nostrils slightly flared. Yet Riddle's bemusement didn't waver.

"No, I expect you wouldn't," his voice was smooth, unruffled by the tempered blade at his throat. The very steel that nicked his flesh slightly as he spoke, a few dots of ruby blood slicking the silver edge. 

"Do you have anything to say for yourself?"Her tone took that of frustrated disgust. Eyes as black as his polished boots, and just as mirrored, pinned her with intensity. 

"Yes," he grabbed the steel of her cutlass, and her eyes widened despite herself as the red poured from the hand that gripped the sharpened blade. 

"You're much too naive, Miss Granger, if you think you were brought here of your own motive and accord," he grinned wickedly, twisting the blade in a deft and unexpected move, her primary defense clattering to the wooden ship deck, the blade painted a gruesome crimson where his hand had held it.

Hermione swallowed but moved for her pistol, only to find her very own firearm jammed into the soft underside of her chin. Honey eyes screamed with retribution as he tutted her error. 

"Don't be so boring," Riddle ran his knuckles down the assassin's slightly sun freckled cheekbones in a unnervingly intimate gesture. "I'm not going to kill you. Not so quickly."

His black eyes glittered coldly, "Unless you force my hand. So be a good girl, and disarm yourself."

Hermione scowled, baulking. He shoved the gun into the bottom of her jaw with malice. 

"I'm being very patient, kind even, Miss Granger, I could always search you for weapons myself." At the threat she swallowed hard, jaw working against the pressure of the gun muzzle pressing into the underside of her chin. Black eyes danced with mischief. Captain Riddle would search her indeed. So well she feared there wouldn't be a scant inch of her person left unexplored. A shiver of something best left unmentioned crawled up her spine.

"That won't be necessary," she uttered frigidly, biting the cold into her words to belay her warmed cheeks. Nimble fingers plucked the blades from her blouse and hip, as well as the small pistol from her ankle and razor sharp chopsticks from her messy bun. The chocolate haired assassin handed them over with begrudging trepidation. Black eyes surveyed her every motion in lazy, predatory satisfaction.

There was only one fate awaiting her. Only one way Captain Riddle dealt with a threat to his person, ship or plans. Flirting aside, the way his black eyes mixed her up and his gentrified charm was all an act. The man before her was a pirate, and a murderer. He didn't want her. Or if he did, his desire to eradicate any threat was sure to take precedence. 

"Good, Miss Granger," he approved in caustic candor, "Now put your arms behind your back."

"You should just be done with it, every second I breathe I pose a threat to you, and your crew," she spat, shoulders defiantly thrust back, chin tilted despite the gun, her mouth a thin line of grim resentment. Captain Riddle had the gall to laugh. A thin, brief chuckle at her innocence. How had such a creature become a weapon against him?

No matter. He was an expert at recrafting weapons to suit his purposes. And what a weapon she was. Buxom, but with a flat stomach and delicate features, not a conventional beauty, but something too lovely was always suspect in his line of work. Not to mention she had such wide, guiliable brown eyes, and pouty lips that begged to be swollen, roughed by his mouth and teeth. Her breasts pushed her tunic, teasing him as he took her slender wrists in a punishing grip, tying them tightly and expertly with a bit of rope behind her. 

"I like you like this, tied up, at my mercy." He breathed against her neck, delighted at the crop of goosebumps that raised on her slightly sun browned skin. This was no pale, placid lady. This woman had callouses and freckles. Yet she was soft in ways he couldn't fathom. It didn't match up. 

"Don't gloat, it's tacky," she advised snootily. His grin was pure evil as he caught a fistful of her wild, springy curls, his black eyes glinting beneath amused brows. He pulled and twisted until she grimaced and squirmed slightly, feeling an acute sense of satisfaction at the sight.

"Don't get cute, Miss Granger, it doesn't suit you," his words, bit out by impossibly white teeth, made her sweat run cold despite the humid night air. "You're in my care now, perhaps you should seek to endear yourself to me." The dark haired villain provoked silkenly. 

Hermione let out a laugh that was more of a barked cackle. Her dubious expression said it all. "I can imagine what the pirate Voldemort does to his would-be assassins. I doubt any civility on my part can dissuade you."

"Oh?" Riddle smirked. "So you know me so very well that you even can predict my motives? I think not, Miss Granger," he chided mockingly, twisting her by her caught hair so she could see his falsely aristocratic profile in all its chiseled splendor. To do so the bastard wound the mass so tightly unintentional tears sprang in the corner of her eyes. But even they they couldn't blur the miserable demon's unholy beauty. High cheekbones, nearly gaunt save for the pleasing way they enhanced his wickedly soft lips and glinting bedroom eyes. His hair was rakish, but artfully so, ribbons of black tendrils that framed his face, a long dip of bangs falling over his left eye. His clothes were impeccable, black on black, with severe shining silver buttons. He looked the very part of the villain he played. Decadent sin in the flesh.

"What can you possibly get from me?" The practical woman challenged. "I'm no noble's daughter, my father is a simple merchant. I have no value."

"Tsk, we shouldn't sell ourselves so short, Miss Granger, your sword skills are quite impressive. Not just anyone could have wrenched my blade from me," he mused, a frown marring his mouth at the begrudging mention, "Besides which, I find myself most reluctant to end our acquaintance on such abruptly gruesome terms."

"So why don't you just contemplate all the possible meanings of being my captive," he suggested to her in a mocking dig that wormed through her in dark tendrils, "Because you are, you know. Mine." His amusement provoked her, exactly as he had the intended it to. Hermione struggled in her bonds, the rough rope scraping against her wrists. 

"Shhh," he grinned against her throat, holding her by her neck instead of hair, a squeeze of her jugular and the sadist reluctantly subsided. "I'm going to treat you far better than you deserve, my little killer."

"I'm not-I-I- haven't…" Hermione gritted her teeth and forced herself to stop being a ninny, "Killing you would be no crime. Besides I've never murdered anyone innocent."

"Oh I know. You haven't actually killed at all, I would have smelled it on you. How brave, Dumbledore is, sending such a green blade," he nuzzled the hollow of her neck, Hermione stiffened. Her instincts screamed danger. This was the Voldemort, not the magnanimous Tom Riddle, slight despot, yet still bound by social etiquette. No, this man who called himself Lord Voldemort, was but a brutal, blood thirsty, perverse pirate. A man who killed and tortured without breaking a sweat. And somehow he knew she worked for the man in the Royal Navy charged with his capture. 

"I was going to be your first. How fitting," he mused, his fingers threaded into her hair again, he seemed obsessed with it. Or maybe it was just how he controlled her with it. Leading her about. The man was a menace, and a bully. 

The brunette girl scowled, nearly ripping her hair out to shoot him a scathing look over her shoulder. He liked that too. How stubborn she was. How devote. If he could pervert that loyalty, twist it to himself, she would never waver, never doubt. She would be his, irrevocably. 

"Go fuck yourself."

He smirked, his barritone voice going gravelly rich, "Oh, Miss Granger, why would I possibly entertain that past time I when I have such a choice alternative at my mercy?"

Her swallow was audible, fingers twitching for the weapons she'd surrendered, wrists bound and eyes saucer wide. 

"Hmm," he tilted his head at her, grinning cheekily with dead, flat black eyes. "Don't worry, sweet, when I take you, and I will take you, it'll be because you're begging for it."

He chuckled at her aghast expression, "Of course, I plan to introduce you to why you will beg, shortly."

"Y-you can't be serious."

"My dear Miss Granger, are you blushing?"

"No!" Her hot denial turned her cheeks even redder. 

"My sweet little prize," he purred. His fingertips whispered across her cheekbones, lips, tracing their outline, and dripping down her chin to graze her neck, the angry woman felt her stomach churn as he played lightly at the hem of her tunics v-cut. To her mortification, the sensation wasn't entirely unpleasant. There was hate, yes, and fear, but somehow those emotions brought a sharper edge to his touch, to the cruel seductive gleam in his fathomless black eyes. 

"I am entranced by you," he mused, his hands glided down her arms, tugging playfully at her bound wrists. "I can't wait to taste you."

"You're a vile, wretched excuse for a human being, a murderer, a pirate, and worse," she all but snarled desperately. 

"Yes," he agreed in bemused candor, "I'm all those things."

"And yet," he tucked a thick tendril of russet curls behind her ear, almost tenderly save for the velvet menace coating his tone, "You still get wet at the very thought of my hands on you."

"In your dreams, Captain Riddle," Hermione scoffed. His hands, larger than they seemed, possibly due to his long fingers, wrapped her waist. She sucked in a shaky, fortifying inhale. His index finger began tracing an intricate, fathomless pattern, and despite herself she felt her body sway, memorized by the soft, teasing touch. 

"In my dreams," he uttered in dark provocation, "You're naked, writhing beneath me." He tugged her bound wrists, an intentional reminder of her vulnerability. Hermione gritted her teeth. Wanting to hate it, the weakness, his smugness, she turned her face away as his tug of her tied limbs seemed to pull at deeper, darker parts of her. His words were disgusting, but they sucked her in, her pert nipples pressing against the thin cotton of her tunic. 

It had seemed practical, the loose white tunic and tight brown breeches, but now they left her figure much too exposed. Providing none of the mystery that layers of gown and petticoats might have. All she'd considered was ease of movement, something that wouldn't bunch or trip her in the event of a hasty escape. But now the clothes seemed a poor decision indeed. Riddle's deft fingers skimmed down her tunic, tracing her luscious breasts. He avoided their peaks, merely stroking the underside and top most curve. He gripped her hips harshly, pressing against her in a highly inappropriate manner, she felt something hard, masculine and demanding pressing against her buttocks. 

Sucking in a shallow gasp, she went to break free, but he clicked his tongue at her in disapproval. "Really, Miss Granger, you'd think you'd never had a proper fuck."

At her hot cheeks and the way she immediately avoided his pinning black gaze Riddle could only raise his eyebrows and gaze around, as if forgetting he was the only one privy to this display. Could it really be? The provocative Miss Granger with her painted lips, thickly lashed honey eyes and pert, soft breasts, how could she not have been touched? She wasn't a coveted noble bred princess swathed in comfort and frills, but her features and attributes were too pleasing to have gone entirely unnoticed. How had such a ripe fruit made it to his clutches untried? 

Greedily, awe well hidden, Riddle sneered, showing no outward sign of intrigue. "Don't tell me you've never been with a man, I'm not an idiot."

"Of course not," her indignant denial was almost proof enough, but she had to embellish. "I have a lover, actually, many lovers." Hermione deflected, desperate to hide this weakness. What sort of woman lived to nineteen without knowing a man? She thought of her benefactor, Lord Harry Potter, and his particularly harsh way of dealing with her potential 'suitors'. He'd made her agree when she was young, too young to understand, and enforced the terms mercilessly. That any beau would have to best him in a duel of swords or pistols in order to grant his Blessing on any man sharing her bed. None had passed. To be fair, not many had tried. She wasn't some beauty who inspired such acts. Especially when pitted against a swordsmanship of Lord Potter's reputation. So here she was. Trying to kill a madman, and also, shamefully virginal. 

But he didn't need know it. Riddle felt his infamous temper enflare. He knew she was lying. There was no confidence in her words or gaze, but it incensed him all the same. Imagined men, touching her, sucking her pert nipples, sliding themselves in her warm, tight heat. Before him. As if they had the right. As if any would dare, now that he'd claimed her as his. 

Captain Riddle wrenched her by the wrists, with little ceremony he tossed her over his shoulder. Hermione's indignant protests falling on deaf ears as he carried her across the deck and down the shadowy hall much like a sack of grain, all but throwing her onto the bed once they reached his cabin, black boots using his heel to slam the door. Breath whooshed out of her, thick curls flying over her face, but not so much that he didn't see her incredulous glare. She tried her bonds enthusiastically, baring her teeth. Gratified by her response the dark haired buccaneer merely smirked, making a meal of taking off his jacket and shirt. His impressive pectorals and sleek, well muscled stomach displayed in the vibrant moonlight. He stood before her in pair of black breeches, looking devious and demanding, a gruesome skull filled with snakes coloring his left bicep, ink marked there by bad men in a dark place, a hell he'd made to ensnare them. 

Whetting her lips, Hermione twitched on the bed, rising as if to leave. Dominance rippled from her captor, dark eyes slicing through her.

"Stop," she shivered at the way his voice could simultaneously seduce and threaten. Both silken scotch, potent and intoxicating, and hard nails, driving and pinning her in place. He forced her gaze to his own, cupping her jaw in a cruel grasp. Honey irises meeting dark depths that swirled in secret delight as he reached for the wide eyed captive positioned on his bed. Captain Riddle pulled her wrists up, far above her head, pinning her in place as easily as a butterfly on a cork board.

"Soon you'll say more, please master more," he promised and Hermione felt terror rise like a icepick down her spine. "Mmmm," he groaned, licking a soft, hot trail up her jugular. His teeth nipped a particularly sensitive part of her neck, causing her to shudder unintentionally. "You taste so innocent."

"I-Im not," the trapped woman insisted, somewhat desperately. 

"Yes, you are," he was so amused she wanted to claw out his eyes, perfect black orbs that they were. "I can't wait to defile every virginal inch of you. I'm going to pervert every delicate, sensitive nerve you have, make your flesh crave the lash of my tongue," he licked a careful line up her throat, causing her to tense, her eyes flaring disgust and deep beneath that, angry arousal. "My cruel touch," with no warning he plucked and twisted those sweet teasing nipple peaks. "And my sweet cock," he rocked the hardness against her inner thigh, his lazy lidded eyes gleaming as she gasped in shock, both at the sensation and crude imagery of his words. "I'm going pervade every sweet orifice you have, my dear, and I'm going to be utterly indecent, and make you love it." 

His hands toyed idly with the strings of her loose tunic, and as he did so Hermione regained her fraying senses and fought. She thrashed wildly. Twisted and bucked. Riddle seemed to sharpen into a more predatory presence at every pressed down limb, eyes glittering as he pinned her tied hands and settled over her, his hips pinning hers down, a thick warning pressed against her thigh. He licked his lips, eyes fixating on her heaving chest. 

"Miss Granger, while your capulation is inevitable, I do appreciate your making this entertaining for me," he murmured darkly, "Your resistance makes this so delectable." He kissed her, softly, lip to lip, and the captive woman shuddered. 

"Glad someone's enjoying themselves," she uttered in a forced dryness. He smirked. Hermione felt her skin tingle, that stare. Like he was eating her with his eyes. Devouring. Savoring. No one looked at her like that. That Captain Riddle should, a horrible, honorless monster, it should make her feel nothing. But her nipples pebbled hard, beckoning despite all reason. The sensitive flesh of her neck tingled still with his wet caress. Warm and fierce. She didn't understand these feelings, this hard, almost painful throb building inside her body like a tight hot coil, made her temper flare. 

She twisted, writhing in his grasp, having no idea how telling it was. He stared down at his prize. A monument of tousled chestnut curls, flushed cheeks, heaving breasts, and honey almond eyes, made dark and lidded by a unknown lust. A more experienced woman might understand, might be able to use the frustrated desire to her advantage. But not his catch. She was smart, recklessly brave, and sadly yet perfectly utterly inexperienced with men. The last fact would prove her at his mercy in ways she had only begun to fathom. 

Usually, he didn't bother with green girls. He liked it dark and rough, so hard a fresh little girls could hardly take his attention. But Miss Granger had asked for it and more, he didn't have to be careful. She wasn't a whore he'd have to pay damages on. She was his. His precious little victim. Needing punishment. 

Riddle wanted her to like it. That would make it so much worse for her. Whimpering and mewling under a man she sought to kill. Even if she managed escape, and such a thing would only transpire if he desired it, she would feel the pain of having moaned for him. For having wanted, no, needed his touch. For having liked every wicked, degenerate thing he had iñ store for her. The prim, proper Miss Granger, made his eager whore. 

His fingers teased the swell of her breasts, noting her shallow, sucking breaths as the dark haired tyrant deliberately skimmed close to but never on, her aching nipples. Riddle grinned as she squirmed and wriggled. Subtle, twitching motions, but he noticed it nonetheless. Despite her fierce glare, she was his already. Needy, pliant. In reward, his hands tugged down her tunic roughly, pulling the fabric down beneath the soft swells. 

His finger tipped one perky, rose hued nipple, a candid tease before began flicking and pinching it with vigor. Hermione wriggled desperately, trying to wrench her wrists free. But her pants weren't entirely from exertion, he noted her dilated pupils, her panicked desperation only party out of fear, as shamed desire warmed her flesh. Her sweet nipples beckoning him like ripe berries. His hot mouth enclosed the teased peak, a smirk curving his mouth as he sucked deep, causing a throaty cry of outraged pleasure to erupt. Only to flick the pebble with his tongue, his teeth clamping as his hand found the other taunt bud and plucked it cruelly. 

"Stop- please-" she begged and thrashed, alternating begging for mercy with cursing him to hell. "You bastard son of a whore!" He grew as content with a cat with cream. Loving her screeching, undone sobs as he made a meal of her sweet breasts. He nibbled, one hand trapping her bound wrists above her head, the other twisting and purely abusing her left nipple as his mouth lavished the right with licks and bites of pleasure. 

Hermione was gasping, tears pouring down her face as her left nipple burned, even a flickering touch a pain against the sensitive areola. Riddle eyes gleamed, looking right into her reddened, tear and snot glistened features as he hungrily suckled on her right tit. The fire there made her stomach burn and legs tingle. She hated it. 

"Pleasure," he mused, finally releasing her breast and responding to her cries. He flicked the left nipple, and she whimpered, it hurt, so why did that also throb? So deeply inside her it scared her to admit it. "Pain."

"I'm going to teach you how intimately I can join the two. This is merely a tease," his black eyes mocked her as he lightly rubbed her wet right nipple. "As a woman of your vast experience might have guessed. The depravities of the flesh I have in store for you, my sweet little prize…" Riddle twisted the right nipple until she began to squirm and tear afresh. "Are only beginning."

Hermione couldn't fathom a worse humiliation. She wouldn't bare it. She couldn't. Riddle lightly kissed her mouth, too quickly and chastely for her to properly react and bash his face in. 

"Now, where were we? Ah yes," his eyed her in cold appreciation. "You're tender breasts, so responsive, I really do think I intend to enjoy them quite a bit before I taste you."

"You don't have to do this, you can't, I mean-" Hermione began desperately. 

"Shhh," he placed a finger against her lips before sliding it teasingly to clench her throat, only to take it lower and begin plucking and twisting her right nipple in earnest, his rough fingers abraiding the ripe nub in punishing, painful administrations. Hermione winced. 

"Mmm, such a red, little ripe cherry," he mused, and even his soft lick of wet tongue stung painfully at her raw left nipple. 

"No, it can't, it hurts," she babbled and pleaded, letting out a whimper as he twisted her right nipple in a particularly mean way. 

"Yes, it does, but I'm going to show you pleasure in pain, Hermione, and first," he mused in dark satisfaction, "I must teach you to love pain."

"You're a filthy, rotten-Ah!" Her cry escaped in a hoarse sob as the rakish degenerate closed his mouth on the red peak of her raw left nipple, suckling it again and again mercilessly, pulling on it and kneading the overly sensitive flesh between his teeth. Her flesh sparked. The pain was there, merciless, sharp, and it lent to the pleasure in an evil way that made her want to scream. So she did. She screamed and sobbed, hating that Riddle seemed to revel in it. His teeth nipping harder as she begged him to stop. His fingers plucking more feveredly as she called him every slur she could think of, and some that made little sense. 

He hummed as her sobs grew more, her fight less fierce. That wouldn't do. Besides, he admired her bite marked pale breasts, the nipples painfully raw from his play. So pretty. All his. He kissed each reverently, a light blessing before he truly defiled his little prisoner. As soon as he touched the ties of her breeches, her alarm grew to terror. She fought him like a wild thing, as if the last hour of torment and exhaustion hadn't transpired. Desperate adrenaline, and he enjoyed tying her slender ankles to his bed post all too much. 

Her arms, already tied, fought and pummeled at him uselessly. A tirade he allowed because he knew she was already well tired. After the last drop of adrenaline faded, she would be a lot more tepid. Easy to manipulate. Her ankles were bound in short order, in any case, seeing as he ran a ship, rope and knots were something he was intimately familiar with. 

"Shhh, be still," he mockingly comforted her, pushing her back onto the bed by her throat. The little minx snarled at him. Bucking. He hummed a little as he tied her bound wrists to the middle of the bed, completing the picture. His little prisoner, completely tied and at his mercy. 

"Riddle, of there is one ounce of decency in you-" she began, obviously trying to reason with him. He snorted.

"There isn't," he assured her, cutting her off with a sneer. "Besides, I'll keep my word, Lady Granger," he look was condescending, "You won't have me inside you until you beg. However, I never said I wouldn't taste the wares. You understand," he began plucking the strings to her breeches, "how can I assure my men you're worth in my bed is equal to your treason unless I have a full understanding of what I'm getting."

"I knew you were a foul, loathe some murderer, but this?" Hermione's disdain poured from her, "A rapist to boot?"

"Oh, this isn't rape," Riddle denied easily, daring to tut her like a child, his fingers sliding the rough trousers down her tauntly bound thighs and calves. "This is an education, Miss Granger. You want to play with dangerous men, you want in on this level? Murder, treason, intrigue," he gave her a chilling regard, yanking her trousers the last bit towards her ankles. 

"This is how I play. For keeps. And I do mean to keep you, my little prize," he ran a finger between her breasts, dipping into her navel before he touched a part of her even Hermione hadn't explored, her womanhood. 

His fingers slicked her silken heat and his eyes grew molten, half lidded. Yet the predatory gleam remained. He teased a small little nub she hadn't known existed there softly, amused as her eyes widened in dubious wonder. Legs splayed and secured, she could do nothing as he idly dipped his fingers into her sweet juices, a throaty cry of disgust escaping her pert mouth as he pressed them into his lips for a taste. Musky sweet. Heaven. His nostrils flared and she began babbling something about cutting off his manhood if he didn't release her.

Cheeky, but oh so sweet to taste. So innocent. God, how he loved destroying fresh, pure things. His tongue found her clit in one sweep, but he licked again, teasing her entrance, probing it for more. Every drop was her defeat against him. Her weakness at his skill. It tasted like pure power over her, and he basked in it. His lips, teeth and tongue nibbling every crevice, lavishing her throbbing clit with long languid teases and punishing nips. 

He rose from her sweet center reluctantly, and seeing her tears, couldn't help but taste those too. Bitter and salty. Like the storms of the sea. She hiccuped, but there was a lidded look to her scowl now, fatigue was winning, her defenses slowly crumbling after only a few hours in his bed. What would she manage when he kept her here for days? Barely allowing her to sleep or eat without him inside her. Fucking, tasting, teasing and hurting her until she was putty in his hands. Just a hot willing hole at his mercy. He wanted to know. To see that. To break the proud Miss Granger into a slut toy, maybe then, when she was just a mewling hungry thing, he'd sell her, or give her to the crew. They had been so good as late. 

"Now Miss Granger, you're right, I have been neglecting you." He sighed as he rose, shaking his head. "A woman of your standing, your skill, deserves my best. And those sweet tits have only begun to know the meaning of being mine."

"Have you always been a monster?" She wondered in weary disgust. He nodded candidly, not bothering to voice his answer, humming as he made a show of searching his special ardmoire, which held a collection of delightful things from his travels A whip? He let her see it. Let her know, but shook his head and replaced the braided leather. Next was a bulkly, oddly shaped device, like a cucumber, but covered in a smooth leather. He replaced that as well. Next he pulled out two small silver things, nearly the shape and size of cufflinks. Pressing one end let the other make a clicking sound and Hermione frowned. 

Utterly vulnerable, her most intimate parts exposed to a madman, and having been systematically terrified and violated, it seemed Riddle was no trifling sadist. He made a true feast of every violation. Even in her darkest nightmares, this sort of horror hasn't occured to her. Maybe that meant Riddle was right, she was foolish. But self pity and rage, while self satisfying, were draining from her, she was exhausted from crying and screaming. Her body feeling an odd fuzzy disorientation from Riddle's mouth on her. Her veins still pinging slightly with the aftershocks. 

The villain in question approached and she stiffened, recognizing that truly lustful look in his eyes to mean he meant to hurt her. When he wanted to make her squirm he was satisfied, yes, but when he hurt her...She shivered in trepidation, there was a sort of immense pleasure in his features. 

"These are quite special, you know, hand crafted," he snapped one silver clamp, it was delicate, almost dainty. "I expect you'll come to appreciate them as I do." His silken barriatone was conspiratorial candor, "Oh dear," he eyed her nipples, still red but not half as stiff or elongated as he knew they could be, "You're shamefully unprepared for my thoughtful gift," he frowned, "I suppose it's my duty to help."

"Tongue or fingers, my little prize?" At her confused stare, he sighed and elaborated, "I'm going to tease those sweet nipples of yours again, and I was being generous and offering you a choice."

Hermione felt she should tell him to go to hell, meant to, she was certain, so why did her traitor voice mumble in shame, "Fingers." At least his hands didn't consume her. His mouth, so hot and fierce, seemed to suck deep, dark feelings from her flesh. 

"Right," Riddle nodded, "As my lady wishes." He took her right nipple first, his lips latching on and his tongue teasing the tip. Hermione sighed, half defeat, and half something she didn't want to admit. 

"Mmmm," the sound traveled across her peaked flesh, "Good girl, I might even let you cum." He sucked the peak harshly as punctuation, delighting as her back arched, but not to fight, the breast offered at a slightly higher tilt than the other. His little prisoner was sliding into an erogenous area of self. A place where she was just wet, soft flesh, and he was in charge. To reward her he plucked her left nipple with his fingers, grinding and twisting it until she whimpered. Then he switched. 

After a moment he pulled back, satisfied with the reddened peaks. He clicked the clip, reminding her of its purpose, and hazy, half lidded amber eyes took it in slowly, her throat hazarding a hard swallow. 

Riddle teased the cool metal against the enflamed flesh, still sticky with his saliva, like a wet glittering fruit. The clamp pressed softly on either side of nipple, and he slightly released the pressure, teasing her with a small nip of it, before letting the clamp bite home. Merciless. Pinching. A fire of pain that made her writhe. Riddle hummed at the spectacle, idly teasing the free nipple as she cursed. 

"You have quite the mouth, filthy, I can't wait to put it to better use," he mused idly. "But we're learning about pain and pleasure now, and this is as I've said, just a preview, my little prize."

Riddle waited until she settled into it. Absorbing the throbbing pain of her clamped flesh, wriggling in shame as it started to restir the other fires he'd ignited in her. A cool touch of metal on her left nipple had her seizing in dread. Reminding her he wasn't finished hurting her yet. 

"This one is my favorite," Riddle decided, thumbing the red nipple and planting a kiss on it's tender peak, "I'm going to treat it special."

"There's something wrong with you," Hermione snarled. 

He chuckled darkly, "Of course there is, but I don't mind it very much," he confided easily, "It serves me well." He attached the second clamp as punctuation, but this time he held the clamp, twisting and flicking it, not giving her time to adjust. He didn't stop until she began to beg for mercy, tears in her eyes. Then he did the same to the right until she begged again, those tears falling so sweetly. 

"Good girl," he petted her mussed hair back from her tear stained face, flushed molten from pain. He loved the way she reacted. So passionate. "Permit me a kiss, and I might release them." 

Hermione nodded quickly and he hid a smirk. Bending down, black eyes drowning her, he took her mouth, plundering her tongue. His mouth on hers was rough and toxic, but also dizzying. He barely allowed her to breathe, taking and taking, giving only what he deigned to. His greedy lips bruised her, tongue stroking and choking her as he thrust it too deep, only to stroke and lauve in turn. Twisting her in knots, using her with reckless abandon for his own selfish whim. 

By the time he released her, her head swam, black splotches eating the sides of her vision. 

"You said-" she began, as he began slowly moving down her, hands stroking her inner thighs reverently. He plied her sweet cunts lips wide open with his fingers, shamelessly so, and licked a possessive trail along the length of her. At her words he paused and snapped his head up. 

"That I might release your sweet nipples, and I might, once you cum for me, my little prize. At least three times," he decided with a nod to himself, "Yes, you won't be allowed respite with less than that."

"If you dare to fall asleep, or fail to please me obediently between then and now," Riddle warned, a feral glint to him, he tweaked her numbed, clamped nipples. It cause some pain now, quite a bit to judge by her squirming, but he knew the true torment would come with their release and the longevity of their capture would determine the amount of pain, "Then I can absolutely promise you, you will wear my pretty jewelry until tomorrow eve, and we will begin your lesson anew." At her horror stricken face he chuckled, "Come now, you claimed to be a fair student," he teased mockingly, "Am I not a fair teacher?" 

"Tell me I'm a fair teacher," he advised darkly, dipping a finger in her sweat heat and teasing her core. He ran it round and round, before sinking the digit deep, growling as he felt a thin membrane tease the end of his forefinger. Her center clenched and reeled at the contact, drawing a tingling awareness to the dull, constricting throb of pain in her nipples. The sensation combined, pain and pleasure, made her gasp. 

"Y-you're a fair teacher," she snapped without a hint of submission. He grinned. 

"Good girl," he stroked the digit he had inside her womanhood up and down, softly withdrawing and plunging down with a harsh snap, his thumb joined the tempo, grinding her sensitive clit harshly. Hermione felt each plunge strike through her like a current. Like the water was rising and engulfing her, merging her skin to a wave of feeling she was drowning in. When he flicked her clamped nipple, the added pain drew a whimper, but this wasn't of despair or anger, but need. What the hell was he doing to her?

Making her like it. As promised. The heathen. 

Hermione wept for what felt like the millionth time in a few hours, and also a hellish eternity. Not prone to tears, his ability to jerk them from her, his delight in them, was pure humiliation. Yet he was using his tongue now, licking and nibbling, and her cries to stop jumbled, became more like encouragements, though the words themselves never changed. She knew he knew, could somehow tell, and yet she was fast forgetting why she must care. Proof that this was devil's work. Utter sorcery. 

"Please," she would beg, and he would teeth her clit until she squirmed, a terrible tension building in. "Stop," her hoarse voice rasped, and he added another finger inside her, plunging faster now, harder. Her thighs jerked, ankles rubbing raw from the ropes. He added a third finger and she keened, the noise almost animal. 

"That's right, my little prize," he purred, rising to her ear to murmur the words, his fingers still eagerly thrusting in her, "Feel how I undo you, wreck you." Hermione whimpered as his teeth and tongue traced her neck, pulling on a part of it that caused her to clench hard against his invading fingers. She was dripping down his hand, so wet and hot he wanted to plunge in her and be done, but that wasn't how he played. 

"Cum for me, little prize," he coaxed, twisting her clit, and she did, shuddering around him violently with the force of her first ever climax. Tossed astray by pure sensation, her whimper more of a scream, and he didn't relent, still plunging and twisting. It was too much. She writhed and tried to subdue it, but he shoved deeper, flicking her clamped nipples and teething her throat. The tidal wave never softened, it stayed hot and throbbing, her slicked skin painfully sensitive as rough fingers curled inside her, finding a new sensation that briefly drove stars behind her eyes, and stoking the need anew. 

"Again." 

Impossible. She'd die. 

"Please," she began, wondering why she bothered, "I can't."

"You will," he assured her confidently. He twisted a clamped nipple to remind her why she should want to, "But this time I plan to taste it."

He pulled out his fingers, pressing them, dripping, against her mouth. Her disgust made him chuckle. 

"Lick them clean, or I'll put something even less pleasant in that sweet little hole," he threatened. Hermione reluctantly opened her mouth, expression pained as she obediently cleaned each finger. Sucking and licking in a way that made his cock throb. 

Maybe tomorrow the whip. They always liked his cock quite a bit after tasting the whip. But tonight was all about teaching her how weak she was. Getting him off wasn't on the schedule. Well, not that way, in any case. Her sweet mouth would have to wait. Once she finished to his satisfaction he kissed her again, pleased as she decided not to fight, even though she stiffened and remained passive as ever in the exchange. He kissed down her throat, biting her breasts softness, licking the flesh inside the clamps with an artful tongue, before lavishing her navel in a preview of what he planned for her sweet clit. 

The dark haired devil nibbled the tender nub, drawing it from it's hood of flesh with sweet licks, before biting it meanly. She jerked, and whimpered. Tired but still too uncomfortable to allow exhaustion to claim her. She thought Riddle had used his mouth on her before, but that was just a tease. He attacked now with raw intent. Licking, suckling and tormenting until she jerked helplessly in her bounds, raw skin bleeding slightly into the rope as he lapped at her flesh, tongue diving deep and teasing her into a mewling squirm. Mindless. Spent but unable to rest. Overwhelmed and overbalanced. 

His finger plunged into her and she breathed a sigh of almost relief, hoping he would stop all the horrid teasing and release her again. The building tension was somehow worse this time. Strung more tauntly and felt too deeply. Her cry of alarm as he removed it and shoved the slick digit into a new hole, her soft anus, was music to his ears. His grin forming against her clit as he bit it in reprimand against her cries of no. Whatever he wanted, she would give. Nothing was too much. Too far. Best she learn. 

The finger in her ass was too crude, her cheeks flamed and shame ate her, even as the digit became part of the perverse song Riddle played on her body. A tune he knew too well, and she too little. He slid it in and out, causing her to clench her sweet cunt, juices running hot and sweet on his tongue as he licked and bit at her sweet flesh. His thumb found her womanhood, working with the index finger in her ass, his mouth devouring her throbbing clit. 

Hermione bucked and cried out, too spent to usher any more tears, her body spasming wildly as he brought her to another bone melting release. Her nerves shooting gun powder and her legs numb and trembling as she came down from the second high. 

As she lay there, an obvious puddle of spent desire, Riddle admired his handiwork. Who would have thought his prim; would-be noble daughter would be an assassin for hire? And that the same girl would have such a dark side under her right corset and innocent flesh? Not every girl Riddle used liked the way he used them, not that it mattered. But he found himself pleased in a way he didn't care to examine that Hermione had succumbed to his touch so wildly, and yet so completely. 

Her pale skin was a patchwork of red marks and teeth imprints. A few bruises were forming on her hips and thighs, her lips swollen, eyes red rimmed and glossy from so many sweet tears. Such a pretty little conquest. He hummed as he untied her ankles, tracing the bleeding rope burns with pleasure. Next were her wrists, and she remained passive, a limp, helpless doll under his administrations. 

Long fingers traced her still damp cheek with possessive appreciation. What a prize. Worth the looks from his men, even if he kept her for a while, when he threw her to them or sold her, none of them would have credit to their doubt. So what if he wanted to enjoy his spoils before dealing with profit? Lord Voldemort was entitled to whatever he wanted. And right now, he kissed her lips softly, a mockery of romance, he wanted his little prize. At his mercy. In his bed. 

"You've pleased me," he decided, "So I'm going to spare you a little."

Her look of doubt said she was spent, but not so well that she'd stop being wary of him enough of him to know better. A in all it made for a fun little bit of sport. She knew he wasn't going to spare her. Good. He adjusted his trousers, drawing her eyes to the bulge there, seated as he was on the edge of the large bed, a bed so big it was practically the whole ship cabin save for his prized ardmoire, it was near eye level with her. 

"You won't have to cum again, unless you wish, and I will release your sweet nipples," Riddle arched a brow at her, "Tell your master he's generous."

"I thought you were my teacher," Hermione mused wryly. His expression darkened, fingers closing her throat. 

"To you, I am everything," he uttered coldly, "Your teacher, your master, your capture, your God, your world." 

"More like my personal devil, come to drag me to hell." Her stubbornness, despite her vulnerability, made Riddle both admire her, and all the more determined to break her past the point of being worthy of admiration. 

"That too," he teased her clamped nipples and she shuddered, lifting a arm that dropped back weakly. 

"Too little blood flow over a long period of time has that effect, you won't be able to move your arms or legs for some time," he advised darkly, "You're still helpless, I just removed the ropes for my pleasure."

"Bastard."

"Worse," he mused, lifting the clamp from her tender right nipple and marveling at how she gasped and wriggled. Half in torment, but also half in pleasure. So easily confused, those sensations, and he did so love to blur the lines. He removed the other while petting and plucking the first, pocketing them and sighing in pleasure as he took the first in his mouth, his fingers shifting to twist her left, and rewarded as her back arched at the fierce onslaught of pained pleasure. 

He switched after a moment, and then pulled back. Haughty and arrogant, he slowly began relieving himself of his constraining breeches. The black material was formfitting but the leather butter soft as it slid down his muscular thighs and calves. Her eyes were saucer wide at the length and size of him, it sprang free like a hidden cobra. So virile and angry, pink purple tip leaking, he stroked himself under her inspection, grinning like the madman he was. His gaze pinned her.

"I'm going to put this between your tits, add a bit of oil, and fuck myself to pleasure. I imagine I will ensure those nipples of yours get more attention," he smiled at her horrified attempts to pathetically inch off the bed. Leaden limbs and exhaustion gaining her little, especially since he stood between her and the exit. "But if you take me in your mouth first, I won't put the clamps back on when I finish."

"You never keep your word. You've lied so much already," she spat. His lithe shoulders shrugged, seeming nonchaulant and in charge even naked and holding himself. 

"No, I've ever only said I might spare your sweet tits. And I did free them, but I never swore to keep them so. In all honesty, I love the way your nipples look in my clamps, all red and raw, I want them always like that. Almost bloody from my affection." She shivered, cold and not from the temperature in the small cabin. "I've kept my word each time, so it's up to you. What will it be, my little prize?" His eyes bled pure challenge. 

"You know already," she told him miserably.

"Yes," he agreed in silken delight, "but you still need to say it. 'Please, master, fuck my mouth.'"

Hermione scowled, jerking her head away as her cheeks flamed. "Never."

"Fine, I don't mind either way," he pointed out, eyes glittering. Hermione winced. Was it possible to hate yourself so much? Apparently yes. But her nipples, the pain there, a softly burning agony, the idea of the clamps being on them again… 

"Please," she choked out in self disgust, "master, fuck my mouth."

"Good girl," he pet her hair back from her face, "Now I'm going to put you where I want you, so behave." He laid himself back, pulling her over him, only to push her head down, hard, pressing her cheek to his hot, throbbing cock. 

"Now suck, and remember, the better you do, the nicer I might be about what follows."

Amber eyes flashed him her defiance, but hesitant, swollen lips found his tip, her hot pink tongue flicking the salty slit. He groaned. It wasn't part of the plan, but he couldn't resist. It wasn't a risk, she knew what he was capable of now. Her mouth enclosed on him carefully, lidded eyes sweeping down, exhausting slightly swaying as her shaky arms fought to hold her up. 

With a wicked look, he clutched her hair, holding her up as she began to wilt, and forced her hot hilt of a mouth down, so far she began to choke, and further still. Slowly, he pulled her back up, loving his control of the situation. She wheezed around his size for air, licking slightly as she recovered. He repeated the process, slowly, languidly choking her on his length, before allowing her to sputter and lick at his tip, before pushing her down all over again. 

Only when he felt precum began to spurt did he pull her off, in a sucking pop, smirking as she gasped heavily for air. He flipped her in a quick, dominant motion, reaching for the oil he'd placed on the bed when he had grabbed the clamps. She hadn't seemed to see it, but that had been the point. Focusing her on one horror at a time.

He painted the oil across her soft, ample breasts almost lovingly. Working it into her flesh, twisting her nipples because they had become a bit of a fascination for him. She squirmed so well when he did. He then positioned himself between her breasts, pulling up her head, and growling, 

"Open," pleased as her mouth parted, and he sunk into the hot cavern, driving in a few sweet thrusts before his hand pulled her breasts against his hot length, forefinger and thumbs pinched onto her nipples at latches, popping out of her mouth before fucking her sweet tits until his cum sprayed her face in hot rivelets. 

"Clean yourself up," he advised, pulling off her, "there's a bucket in the corner. Don't mess up my bedsheets." Cold, aloof. A domineering aristocrat as he pulled on his clothes and sneered at her shame. 

Hermione met his soulless gaze and forced her way up on shaky limbs, ignoring him as she found the wash basin and bucket. She couldn't clean his filth off her quick enough. 

"Do you see what you are now?" Riddle jibed, disliking her ignoring him. She didn't hunch and advert her gaze right. Didn't look as humiliated as he'd hoped. 

Hermione twisted her lips upward, shrugging a single shoulder as she met his gaze over it after and assured him pointedly, "Yes. Do you?"

"They all break." He eyed her with certainty, "Every girl in my bed breaks. You'll do so eventually. The longer you sustain, the more fun for me."

"Be that as it may, it hasn't happened yet. You're degenerate pastimes might prove your undoing, it only gives me time," her tone was actually a little snotty, standing before him nude, washing his cum off her. Riddle clenched his teeth, reminding himself she was hardly impressive. 

"I'll remember that for tomorrow," he promised, "I'll make sure you appreciate you're time with me, Miss Granger," he mocked. She laughed, a slightly brittle sound. 

"One does not dare to doubt it, Captain Voldemort."

He slammed the door behind him. She wasn't shocked he wasn't staying in his own cabin. Everyone knew the captain's quarters were just a place for his perversions. Riddle slept on deck, fully clothed and armed, with one eye open, and so the cabin was just a prison. The lock clicking in place from the outside proved it. Only Captain Riddle had the key, so on the upside he hadn't decided to share her with his crew yet. Thank God for small mercies she supposed. 

Hermione tried not to think. Because every thought was a razor blade. Every inhale reminding her of her violated body, ruined reputation, and likely damned soul. Thinking she'd cried all she could possibly manage to, it was with shock that she rubbed her blurry eyes and drew away wet fingers. What would Lord Harry think? All that time put into her protection? She'd failed him, Duke Dumbledore too. Captured far too easily. Turned into a whore within mere hours. 

She scrubbed herself until she felt more than raw, admitting defeat only when the bucket was spent. Feeling too exposed, she hunted down her clothes, her tunic was slightly torn, but she shoved it on, pulling up the breeches and triple knotting the ties. The exhausted, shamed girl then fell into bed, barely managing to pull over the blanket before she passed into a blissful oblivion. 

-*-*-*-

Hermione awoke slowly, to an odd sensation. Languid, disoriented, she felt her dreams swirl slightly into the background as a pleasant tug lapped at her breast. In a sleep muddled state she made a hum of approval. Something soft tickled her thigh and she giggled, moving it away as reflex, a slight stroking between her legs rewarded her, but it was the bite of teeth clamping that pulled her eyes wide in alarm. 

Dark hair obscured her vision, but there was no mistaking the man teething her nipple. 

"Good morning," he murmured, raising his head at her gasp. "You're quite the deep sleeper, I managed to rid you of that ugly tunic already. I'm thinking of burning your clothes," he added by way of conversation, "I prefer you naked, at all times."

"Don't you dare," she tried to jerk away, but he merely pinned her better, hands catching her wrists almost too easily and pinning them above her as his legs caged her own. 

"Give me my favorite, offer it to me and beg me to taste it, and I won't burn them...today," he added the last with a smirk. Hermione felt shame crawl up her neck and cheeks, but thrust her left breast up at the tyrant. 

"Taste it, please," she monotoned, and he frowned long and hard until she uttered begrudgingly, "Master."

"If you wish," he bent his head, using his teeth to clamp hard and fierce. 

"Ah!"

He bit a little harder, so deep she feared he'd bite it off. 

"Please, I'm sorry! Don't please!"

After a moment he released the nub, licking it softly and kissing it once. His eyes bore into her with meaning.

"How you ask, determines how I respond," he advised her. "Surely you realize by now. Or perhaps?" She didn't know when or how he'd undone her breeches, but he lifted off her and yanked them down so fast she could barely process, his finger sliding through her wet flesh in satisfaction, "You enjoy me hurting you."

"No. Never," she denied with certainty. That sort of vile thinking was something only a lunatic like Riddle could fashion. A excuse for his perverse nature. 

"Hmmm, time will tell." Riddle promised. "Unfortunately I'm a busy Captain and not a eager little prize," he pinched her clit, legs forcing hers wider apart as she struggled, "so I don't have time to tie you up and pleasure you, but if you force me to choose…"

Eyes as black as sin itself found hers, his fingers sliding into her as if they belonged. "I will tie you up, clamp you, gag you, and leave you until dinner."

"Still struggling?" He snarled as she freed a wrist in a wild twist, and slapped him clean across his smug profile. A profile which now looked icy with cruelty. "Fine. I guess I know what you like then." He grinned, hand finding her throat and squeezing until she clawed and gasped. 

"Pain it is." He smiled, and it was a beautifully horrific expression, so genuine it was wrong. He made little work of tying her legs and wrists chuckling as she fought and yelled. 

"Perfect," he tied her naked, of course, and he delighted full in pulling a small gag from his armoire and silencing her into choked, incomprehensible garbles. 

He whistled as he selected the the large, wooden bobby pins, showing them to his trussed little victim with relish. "For your insolence," he commented idly. "Slapping me won't be tolerated, ever. To strike your master, of course, you do understand, the punishment can't be light." His silken words lead him to the bed, where fully clothed, he began to idly stroke her nipples with the rough wooden instruments. 

"This is your choice," he reminded her darkly, "I could have been gentle, but you don't like that, do you?" He mused in understanding, she shivered, "You need a firm hand, as I hoped."

He teased her right nipple back and forth, snapping the wood occasionally and making her flinch. Before dipping his head and licking some of the tears off her face. 

"You don't deserve my mouth, but I can't resist you," he sighed, resigning himself to the need to suck and teeth each nipple into a ripeness before latching the rough, heavy wood onto their sweet peaks. 

"When I release them tonight," he petted the bobbing pins as she writhed and begged in garbled words behind her gag, "A mere breathe of air will be pain on them." His tone and expression told her he couldn't wait. 

"Until then, my little prize."

He left her. Tied. Naked. Legs splayed. Womanhood open and exposed. Nipples burning a worse pain than imagined, the clips were nothing. These didn't go numb, not for a long while, and even then, with their weight, every shift of her body brought their pain back to the forefront of sensation. To her shame, a wetness pooled between her legs as it did so, proving Riddle right in a way that made her want to cry. Yet crying moved the clamps, and tears and arousal were too easily mixed in her body. 

He'd only begun to break her.

And break her he would.


End file.
